Thermoset compositions

Abstract

Disclosed are thermoset compositions including a dispersion of a particulate solid into a thermosetting resin in the presence of a coupling agent including a reaction product of at least a reactant A, with a reactant B and / or a reactant C, as described herein. Various methods of making and / or using the coupling agent and / or the thermoset compositions are also disclosed.

Description

THERMOSET COMPOSITIONS

[0001] The disclosed technology relates to a reaction product which may be used as a coupling agent, such as in thermoset compositions including particulate solids.

[0002] The incorporation of particulate solids (e.g., fillers and / or fibers) into polymeric materials (such as thermosetting polymers, thermoplastic polymers, elastomers, and / or rubber) is known; the combination of these materials represent a subset of composite material. Molded articles made from these types of composite materials may exhibit improved stiffness, hardness, and / or creep resistance, as compared with corresponding unfilled polymeric materials. However, these types of composite materials may exhibit a marked decrease in toughness and / or ductility, as compared with corresponding un-filled polymeric materials. In the cases of thermoplastic polymer and thermosetting polymers, composite molded articles may become too brittle, or too low in impact resistance and elongation, to be of much practical use.

[0003] Various approaches have been attempted to improve compatibility of the particulate solid with the polymeric materials to improve such deficiencies. For example, incorporating a surface modifier or sizing agent, such as by coating the particulate solid, may improve compatibility. The surface modifier / sizing agent may generally fall within two categories: coupling agents and non-coupling modifiers. Non-coupling modifiers interact with the surface of the particulate solid, but do not interact with the polymer matrix.

[0004] Coupling agents interact with both the surface of the particulate solid and the polymer matrix. In many cases, coupling agents covalently bond to both the particulate solid and the polymer matrix. In other cases, an ion-pair interaction between the coupling agent and the particulate solid may be adequate, while chain entanglement and / or cocrystallization may provide a sufficient interaction between the coupling agent and the polymer matrix.

[0005] The disclosed technology, therefore, provides reaction products, useful as coupling agents, which may overcome certain deficiencies mentioned above.

[0006] The subject matter disclosed herein provides a thermoset composition comprising a coupling agent comprising a reaction product of at least a reactant A, with a reactant B and / or a reactant C; wherein the reactant A is represented by the following general formula (A):wherein, independently for each molecule of the reactant A:R1is a terminal group;R2is, independently for each repeat unit, H or COOH;R3is, independently for each repeat unit, H, CH3, or CH2COOH;R4is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group;R5is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group;R6is a terminal group; n is an integer from 10 to 1400; and m is 0 or an integer from 1 to 140; wherein, when R2is COOH in a repeat unit, R3is H or CH3 in the repeat unit; and wherein, if m is not 0, n is at least 10 times greater than m; wherein the reactant B is represented by the following general formula (B):wherein, independently for each molecule of the reactant B:R7is a Ci to C15 hydrocarbyl group;R8is, independently for each repeat unit, H or CH3;R9is a Ci to C4 hydrocarbyl group; and z is an integer from 10 to 80; wherein the reactant C is represented by the following general formula (C):wherein, independently for each molecule of the reactant C:R10is a Ci to C50 hydrocarbyl group;R11is, independently for each repeat unit, H or CH3;R12is, independently for each repeat unit, a Ci to Cs hydrocarbyl group; x is 0 or an integer from 1 to 50; and y is 0 or an integer from 1 to 20; wherein the sum of x and y is at least 3 (such as at least 4, or at least 5); wherein substantially all individual molecules of reactant C react with one acid group present in reactant A to form an ester, and / or substantially all individual molecules of reactant B react with (i) one acid group present in reactant A to form an amide, or (ii) two acid groups present in reactant A to form an imide; and wherein the reactant A is present in an amount of from 10 to 65 weight percent, the reactant B is present in an amount of from 0 to 90 weight percent, and the reactant C is present in an amount of from 0 to 90 weight percent, with the proviso that at least one of reactant B or reactant C is present in an amount greater than 0 weight percent, all based on the total combined weight of reactant A, reactant B, and / or reactant C.

[0007] In certain embodiments, the thermoset composition may comprise a dispersion of a particulate solid into a thermosetting resin in the presence of the coupling agent.

[0008] Also provided are various methods of making and / or using the reaction product, the coupling agent, and / or the thermoset composition.

[0009] The following embodiments of the present subject matter are contemplated:

[0010] 1. A thermoset composition comprising a dispersion of a particulate solid into a thermosetting resin in the presence of a coupling agent comprising a reaction product of at least a reactant A, with a reactant B and / or a reactant C; wherein the reactant A is represented by the following general formula (A):wherein, independently for each molecule of the reactant A: R1is a terminal group; R2is, independently for each repeat unit, H or COOH; R3is, independently for each repeat unit, H, CH3, or CH2COOH; R4is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group; R5is, independently for each repeat unit, H or a Ci to C36 hydrocarbylgroup; R6is a terminal group; n is an integer from 10 to 1400; and m is 0 or an integer from 1 to 140; wherein, when R2is COOH in a repeat unit, R3is H or CH3 in the repeat unit; and wherein, if m is not 0, n is at least 10 times greater than m; wherein the reactant B is represented by the following general formula (B):wherein, independently for each molecule of the reactant B: R7is a Ci to C15 hydrocarbyl group; R8is, independently for each repeat unit, H or CH3; R9is a Ci to C4 hydrocarbyl group; and z is an integer from 10 to 80; wherein the reactant C is represented by the following general formula (C):wherein, independently for each molecule of the reactant C: R10is a Ci to C50 hydrocarbyl group; R11is, independently for each repeat unit, H or CH3; R12is, independently for each repeat unit, a Ci to Cs hydrocarbyl group; x is 0 or an integer from 1 to 50; and y is 0 or an integer from 1 to 20; wherein the sum of x and y is at least 3; wherein substantially all individual molecules of reactant C react with one acid group present in reactant A to form an ester, and / or substantially all individual molecules of reactant B react with (i) one acid group present in reactant A to form an amide, or (ii) two acid groups present in reactant A to form an imide; and wherein the reactant A is present in an amount of from 10 to 65 weight percent, the reactant B is present in an amount of from 0 to 90 weight percent, and the reactant C is present in an amount of from 0 to 90 weight percent, with the proviso that at least one of reactant B or reactant C is present in an amount greater than 0 weight percent, all based on the total combined weight of reactant A, reactant B, and / or reactant C.

[0011] 2 The thermoset composition of embodiment 1, wherein the particulate solid is present in an amount of from 20 to 80 weight percent, based on the total weight of the thermoset composition.

[0012] 3. The thermoset composition of either embodiment 1 or embodiment 2, wherein the particulate solid comprises at least one of an extender, a reinforcing material, or a functional filler.

[0013] 4. The thermoset composition of embodiment 3, wherein the extender comprises at least one of calcium carbonate, talc, barium sulfate, alumina, or quartz.

[0014] 5. The thermoset composition of either embodiment 3 or embodiment 4, wherein the reinforcing material comprises at least one type of fibrous material.

[0015] 6. The thermoset composition of any one of embodiments 3 to 5, wherein the functional filler comprises at least one of flame retardant materials or pigments.

[0016] 7 The thermoset composition of any one of embodiments 1 to 6, wherein the thermosetting resin is present in an amount of from 80 to 20 weight percent, based on the total weight of the thermoset composition.

[0017] 8. The thermoset composition of any one of embodiments 1 to 7, wherein the thermosetting resin comprises an epoxide resin, an unsaturated polyester resin, a vinyl ester resin, a polyurethane resin, or a phenolic resin.

[0018] 9. The thermoset composition of any one of embodiments 1 to 8, wherein the coupling agent is present in an amount of from 0.5 to 5 weight percent, based on the total weight of the thermoset composition.

[0019] 10. The thermoset composition of any one of embodiments 1 to 9, wherein R2isH.

[0020] 11. The thermoset composition of any one of embodiments 1 to 9, wherein R2isCOOH.

[0021] 12. The thermoset composition of any one of embodiments 1 to 11, wherein R3is, independently for each repeat unit, H or CH3.

[0022] 13. The thermoset composition of any one of embodiments 1 to 11, wherein R3is, independently for each repeat unit, H or CH2COOH.

[0023] 14. The thermoset composition of any one of embodiments 1 to 10, wherein R3is, independently for each repeat unit, CH3 or CH2COOH.

[0024] 15. The thermoset composition of any one of embodiments 1 to 13, wherein R3is H.

[0025] 16. The thermoset composition of any one of embodiments 1 to 12, or 14, wherein R3is CH3.

[0026] 17. The thermoset composition of any one of embodiments 1 to 10, or 13 to 14, wherein R3is CH2COOH.

[0027] 18. The thermoset composition of any one of embodiments 1 to 17, wherein R4is, independently for each repeat unit, H or a Ci to C20 hydrocarbyl group.

[0028] 19. The thermoset composition of any one of embodiments 1 to 18, wherein R4is H.

[0029] 20. The thermoset composition of any one of embodiments 1 to 17, wherein R4is a Ci to C36 hydrocarbyl group.

[0030] 21. The thermoset composition of any one of embodiments 1 to 18, or 20, wherein R4is a Ci to C20 hydrocarbyl group.

[0031] 22. The thermoset composition of any one of embodiments 1 to 21, wherein R5is, independently for each repeat unit, H or a Ci to C20 hydrocarbyl group.

[0032] 23. The thermoset composition of any one of embodiments 1 to 22, wherein R5is H.

[0033] 24. The thermoset composition of any one of embodiments 1 to 21, wherein R5is a Ci to C36 hydrocarbyl group.

[0034] 25. The thermoset composition of any one of embodiments 1 to 22, or 24, wherein R5is a Ci to C20 hydrocarbyl group.

[0035] 26. The thermoset composition of any one of embodiments 1 to 25, wherein n is an integer from 10 to 250.

[0036] 27. The thermoset composition of any one of embodiments 1 to 25, wherein n is an integer from 20 to 1400.

[0037] 28. The thermoset composition of any one of embodiments 1 to 27, wherein n is an integer from 20 to 150.

[0038] 29. The thermoset composition of any one of embodiments 1 to 28, wherein m is 0 or an integer from 1 to 25.

[0039] 30. The thermoset composition of any one of embodiments 1 to 29, wherein m is 0 or an integer from 1 to 15.

[0040] 31. The thermoset composition of any one of embodiments 1 to 30, wherein m is 0.

[0041] 32. The thermoset composition of any one of embodiments 1 to 28, wherein m is an integer from 1 to 140.

[0042] 33. The thermoset composition of any one of embodiments 1 to 29, or 32, wherein m is an integer from 1 to 25.

[0043] 34. The thermoset composition of any one of embodiments 1 to 30, or 32 to 33, wherein m is an integer from 1 to 15.

[0044] 35. The thermoset composition of any one of embodiments 1 to 34, wherein z is an integer from 10 to 50.

[0045] 36. The thermoset composition of any one of embodiments 1 to 34, wherein z is an integer from 20 to 80.

[0046] 37. The thermoset composition of any one of embodiments 1 to 36, wherein z is an integer from 20 to 50.

[0047] 38. The thermoset composition of any one of embodiments 1 to 37, wherein x is0 and y is an integer from 3 to 20.

[0048] 39. The thermoset composition of any one of embodiments 1 to 37, wherein x is an integer from 3 to 50 and y is 0.

[0049] 40. The thermoset composition of any one of embodiments 1 to 37, wherein x is an integer from 1 to 50 and y is an integer from 1 to 20.

[0050] Various features and embodiments of the present subject matter will be described below by way of non-limiting illustration.

[0051] As used herein, the term “hydrocarbyl” refers to a group having a carbon atom directly attached to the remainder of the molecule, where the group includes at least carbon and hydrogen atoms. If the hydrocarbyl group comprises more than one carbon atom, then those carbons need not necessarily be linked to each other. For example, at least two of the carbons may be linked via a suitable element or group. In various embodiments, the term “hydrocarbyl” refers to a group having a carbon atom directly attached to the remainder of the molecule, where the group consists of carbon, hydrogen, optionally one or more heteroatoms provided the heteroatoms do not alter the predominantly hydrocarbon nature of the substituent. The heteroatom may link at least two of the carbons in the hydrocarbyl group, and optionally no more than two non-hydrocarbon substituents. Suitable heteroatoms will be apparent to those skilled in the art and include, for instance, sulphur, nitrogen, oxygen, phosphorus and silicon. Where the hydrocarbyl contains heteroatoms, optionally, no more than two heteroatoms will be present for every ten carbon atoms in the hydrocarbyl group. Suitable non-hydrocarbon substituents will also be apparent to those skilled in the art and include, for instance, halo, hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulphoxy.

[0052] Examples of hydrocarbyls within the context of the present technology therefore include: (i) hydrocarbon groups selected from aliphatic (e.g. alkyl or alkenyl), alicyclic (e.g. cycloalkyl, cycloalkenyl, cycloalkadienyl), and aromatic groups; (ii) substituted hydrocarbon groups, selected from hydrocarbon groups defined in (i) substituted with nomore than two non-hydrocarbon substituents and / or one or more hydrocarbon substituents, the non-hydrocarbon substituents being selected from the group consisting of halo, hydroxy, alkoxy, mercapto, alkylmercapto, nitro, nitroso, and sulphoxy; and / or (iii) hetero-containing hydrocarbon groups, selected from hydrocarbon groups defined in (i) containing one or more heteroatom in the ring or chain, provided that the group has no more than two heteroatoms present for every ten carbon atoms in the group, the heteroatoms being selected from sulphur, nitrogen, oxygen, phosphorus and silicon. The hetero-containing hydrocarbon groups may be substituted with no more than two non-hydrocarbon substituents and / or one or more hydrocarbon substituents. In certain embodiments, the term “hydrocarbyl” refers to a group having a carbon atom directly attached to the remainder of the molecule, where the group consists of carbon and hydrogen atoms.

[0053] It is known that some of the materials described herein may interact in the final formulation, so that the components of the final formulation may be different from those that are initially added. The products formed thereby, including the products formed upon employing the composition of the present subject matter in its intended use, may not be susceptible of easy description. Nevertheless, all such modifications and reaction products are included within the scope of the present subject matter; the present subject matter encompasses the composition prepared by admixing the components described herein.

[0054] As used herein, the indefinite article “a” / “an” is intended to mean one or more than one. As used herein, the phrase “at least one” means one or more than one of the following terms. Thus, “a” / “an” and “at least one” may be used interchangeably. For example “at least one of A, B or C” means that just one of A, B or C may be included, and any mixture of two or more of A, B and C may be included, in alternative embodiments.

[0055] As used herein, unless stated otherwise, the term “substantially” means that a value of a given quantity is within ±10% of the stated value. In other embodiments, the value is within ±5% of the stated value. In other embodiments, the value is within ±2.5% of the stated value. In other embodiments, the value is within ±1% of the stated value.

[0056] As used herein, the transitional term “comprising,” which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, un-recited elements or method steps. However, in each recitation of “comprising” herein, it is intended that the term also encompass, as alternative embodiments, the phrases “consisting essentially of’ and “consisting of,” where “consisting of’ excludes any element or step not specified and “consisting essentially of’ permits theinclusion of additional un-recited elements or steps that do not materially affect the essential or basic and novel characteristics of the composition or method under consideration.

[0057] Provided is a thermoset composition comprising a dispersion of a particulate solid into a thermosetting resin in the presence of a coupling agent comprising a reaction product of at least a reactant A, with a reactant B and / or a reactant C, as described herein. In the context of the phrase “a reaction product of at least a reactant A, with a reactant B and / or a reactant C”, “at least” means that other reactants and / or ingredients could be present in the reaction, as long as the properties of the resulting reaction product are substantially unchanged.

[0058] In certain embodiments, substantially all individual molecules of reactant C react with one acid group present in reactant A to form an ester, and / or substantially all individual molecules of reactant B react with (i) one acid group present in reactant A to form an amide, or (ii) two acid groups present in reactant A to form an imide. In this context, “substantially all” means that the reaction is designed such that reaction of reactants B and / or C is maximized, but there could be minor amounts of reactants B and / or C remaining unreacted due to slight variations in stoichiometry and / or reaction conditions (potentially impacting reaction kinetics and other factors), as would be understood by a person of ordinary skill in the art. Further, because the reaction is designed in this way, to force reaction of reactants B and / or C to consume as much of those reactants as possible, there will be some unreacted reactant A present in the reaction product.

[0059] The reactant A is represented by the following general formula (A):wherein, independently for each molecule of the reactant A: R1is a terminal group; R2is, independently for each repeat unit, H or COOH; R3is, independently for each repeat unit, H, CH3, or CH2COOH; R4is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group; R5is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group; R6is a terminal group; n is an integer from 10 to 1400; and m is 0 or an integer from 1 to 140. In certain embodiments, when R2is COOH in a repeat unit, R3is H or CH3 in the repeat unit. In certain embodiments, if m is not 0, n is at least 10 times greater than m. Asused herein, the phrase “independently for each molecule” means that a variable may vary from molecule to molecule of a component which is described by a general formula including such variables, thereby forming a mixture of molecules which individually may have a different selection for each variable, but it is also contemplated that the variable may be the same for all molecules. Similarly, the phrase “independently for each repeat unit” means that a variable may vary from repeat unit to repeat unit in a single molecule, but it is also contemplated that the variable may be the same for all repeat units. As would be understood by a person of skill in the art, one or more of the carboxylic acid groups present in reactant A could be in a salt form or an anhydride form without substantially impacting the reactant product and / or its properties, as it is generally known that certain amounts of carboxylic acid groups may naturally form salts or anhydrides.

[0060] In certain embodiments, the reactant A is present in an amount of from 10 to 65 (such as from 10 to 60, from 10 to 55, from 10 to 50, from 10 to 45, from 10 to 40, from 10 to 35, from 10 to 30, from 10 to 25, from 10 to 20, from 10 to 15, from 15 to 65, from 15 to 60, from 15 to 55, from 15 to 50, from 15 to 45, from 15 to 40, from 15 to 35, from 15 to30, from 15 to 25, from 15 to 20, from 20 to 65, from 20 to 60, from 20 to 55, from 20 to50, from 20 to 45, from 20 to 40, from 20 to 35, from 20 to 30, from 20 to 25, from 25 to65, from 25 to 60, from 25 to 55, from 25 to 50, from 25 to 45, from 25 to 40, from 25 to35, from 25 to 30, from 30 to 65, from 30 to 60, from 30 to 55, from 30 to 50, from 30 to45, from 30 to 40, from 30 to 35, from 35 to 65, from 35 to 60, from 35 to 55, from 35 to50, from 35 to 45, from 35 to 40, from 40 to 65, from 40 to 60, from 40 to 55, from 40 to50, from 40 to 45, from 45 to 65, from 45 to 60, from 45 to 55, from 45 to 50, from 50 to65, from 50 to 60, from 50 to 55, from 55 to 65, from 55 to 60, or from 60 to 65) weight percent, based on the total combined weight of reactant A, reactant B, and / or reactant C. Non-limiting examples of suitable materials which may be used as reactant A include polyacrylic acid, polymethacrylic acid, polyacrylic-co-maleic acid, polyacrylic-co- methacrylic acid, polyacrylic-co-citraconic acid, and / or polyacrylic-co-itaconic acid, optionally co-reacted with mono-unsaturated monomers, such as acrylates and / or methacrylates, for example butyl acrylate and / or butyl methacrylate.

[0061] The reactant B is represented by the following general formula (B):wherein, independently for each molecule of the reactant B: R7is a Ci to C15 hydrocarbyl group; R8is, independently for each repeat unit, H or CH3; R9is a Ci to C4 hydrocarbyl group; and z is an integer from 10 to 80.

[0062] In certain embodiments, the reactant B is present in an amount of from 0 to 90 (such as from 0 to 85, from 0 to 80, from 0 to 75, from 0 to 70, from 0 to 65, from 0 to 60, from 0 to 55, from 0 to 50, from 0 to 45, from 0 to 40, from 0 to 35, from 0 to 30, from 0 to 25, from 0 to 20, from 0 to 15, from 0 to 10, from 0 to 5, from greater than 0 to 90, from greater than 0 to 85, from greater than 0 to 80, from greater than 0 to 75, from greater than 0 to 70, from greater than 0 to 65, from greater than 0 to 60, from greater than 0 to 55, from greater than 0 to 50, from greater than 0 to 45, from greater than 0 to 40, from greater than 0 to 35, from greater than 0 to 30, from greater than 0 to 25, from greater than 0 to 20, from greater than 0 to 15, from greater than 0 to 10, from greater than 0 to 5, from 5 to 90, from 5 to 85, from 5 to 80, from 5 to 75, from 5 to 70, from 5 to 65, from 5 to 60, from 5 to 55, from 5 to 50, from 5 to 45, from 5 to 40, from 5 to 35, from 5 to 30, from 5 to 25, from 5 to 20, from 5 to 15, from 5 to 10, from 10 to 90, from 10 to 85, from 10 to 80, from 10 to 75, from 10 to 70, from 10 to 65, from 10 to 60, from 10 to 55, from 10 to 50, from 10 to 45, from 10 to 40, from 10 to 35, from 10 to 30, from 10 to 25, from 10 to 20, from 10 to 15, from 15 to 90, from 15 to 85, from 15 to 80, from 15 to 75, from 15 to 70, from 15 to 65, from 15 to 60, from 15 to 55, from 15 to 50, from 15 to 45, from 15 to 40, from 15 to 35, from 15 to 30, from 15 to 25, from 15 to 20, from 20 to 90, from 20 to 85, from 20 to 80, from 20 to 75, from 20 to 70, from 20 to 65, from 20 to 60, from 20 to 55, from 20 to 50, from 20 to 45, from 20 to 40, from 20 to 35, from 20 to 30, from 20 to 25, from 25 to 90, from 25 to 85, from 25 to 80, from 25 to 75, from 25 to 70, from 25 to 65, from 25 to 60, from 25 to 55, from 25 to 50, from 25 to 45, from 25 to 40, from 25 to 35, from 25 to 30, from 30 to 90, from 30 to 85, from 30 to 80, from 30 to 75, from 30 to 70, from 30 to 65, from 30 to 60, from 30 to 55, from 30 to 50, from 30 to 45, from 30 to 40, from 30 to 35, from 35 to 90, from 35 to 85, from 35 to 80, from 35 to 75, from 35 to 70, from 35 to 65, from 35 to 60, from 35 to 55, from 35 to 50, from 35 to 45, from 35 to 40, from 40 to 90, from 40 to 85, from 40 to 80, from 40 to 75, from 40 to 70, from 40 to 65, from 40 to 60,from 40 to 55, from 40 to 50, from 40 to 45, from 45 to 90, from 45 to 85, from 45 to 80, from 45 to 75, from 45 to 70, from 45 to 65, from 45 to 60, from 45 to 55, from 45 to 50, from 50 to 90, from 50 to 85, from 50 to 80, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to 90, from 55 to 85, from 55 to 80, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to 90, from 60 to 85, from 60 to 80, from 60 to 75, from 60 to 70, from 60 to 65, from 65 to 90, from 65 to 85, from 65 to 80, from 65 to 75, from 65 to 70, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 90, from 80 to 85, or from 85 to 90) weight percent, based on the total combined weight of reactant A, reactant B, and / or reactant C. Non-limiting examples of suitable materials which may be used as reactant B include a poly etheramine derived from a C12 to C15 alcohol reacted with propylene oxide followed by base catalyzed addition of the resultant polyether alcohol to acrylonitrile and subsequent hydrogenation to give an amine, and / or alpha-terminated polyether amines (including but not limited to those commercially available from Huntsman under the trade name Surfonamine® (including, but not limited to B60, Bl 00, B200, LI 00, L200, L207, or L300)).

[0063] The reactant C is represented by the following general formula (C):wherein, independently for each molecule of the reactant C: R10is a Ci to Cso hydrocarbyl group; R11is, independently for each repeat unit, H or CH3; R12is, independently for each repeat unit, a Ci to Cs hydrocarbyl group; x is 0 or an integer from 1 to 50; and y is 0 or an integer from 1 to 20; wherein the sum of x and y is at least 3 (such as at least 4 or at least 5).

[0064] In certain embodiments, the reactant C is present in an amount of from 0 to 90 (such as from 0 to 85, from 0 to 80, from 0 to 75, from 0 to 70, from 0 to 65, from 0 to 60, from 0 to 55, from 0 to 50, from 0 to 45, from 0 to 40, from 0 to 35, from 0 to 30, from 0 to 25, from 0 to 20, from 0 to 15, from 0 to 10, from 0 to 5, from greater than 0 to 90, from greater than 0 to 85, from greater than 0 to 80, from greater than 0 to 75, from greater than 0 to 70, from greater than 0 to 65, from greater than 0 to 60, from greater than 0 to 55, from greater than 0 to 50, from greater than 0 to 45, from greater than 0 to 40, from greater than0 to 35, from greater than 0 to 30, from greater than 0 to 25, from greater than 0 to 20, from greater than 0 to 15, from greater than 0 to 10, from greater than 0 to 5, from 5 to 90, from 5 to 85, from 5 to 80, from 5 to 75, from 5 to 70, from 5 to 65, from 5 to 60, from 5 to 55, from 5 to 50, from 5 to 45, from 5 to 40, from 5 to 35, from 5 to 30, from 5 to 25, from 5 to 20, from 5 to 15, from 5 to 10, from 10 to 90, from 10 to 85, from 10 to 80, from 10 to 75, from 10 to 70, from 10 to 65, from 10 to 60, from 10 to 55, from 10 to 50, from 10 to 45, from 10 to 40, from 10 to 35, from 10 to 30, from 10 to 25, from 10 to 20, from 10 to 15, from 15 to 90, from 15 to 85, from 15 to 80, from 15 to 75, from 15 to 70, from 15 to 65, from 15 to 60, from 15 to 55, from 15 to 50, from 15 to 45, from 15 to 40, from 15 to 35, from 15 to 30, from 15 to 25, from 15 to 20, from 20 to 90, from 20 to 85, from 20 to 80, from 20 to 75, from 20 to 70, from 20 to 65, from 20 to 60, from 20 to 55, from 20 to 50, from 20 to 45, from 20 to 40, from 20 to 35, from 20 to 30, from 20 to 25, from 25 to 90, from 25 to 85, from 25 to 80, from 25 to 75, from 25 to 70, from 25 to 65, from 25 to 60, from 25 to 55, from 25 to 50, from 25 to 45, from 25 to 40, from 25 to 35, from 25 to 30, from 30 to 90, from 30 to 85, from 30 to 80, from 30 to 75, from 30 to 70, from 30 to 65, from 30 to 60, from 30 to 55, from 30 to 50, from 30 to 45, from 30 to 40, from 30 to 35, from 35 to 90, from 35 to 85, from 35 to 80, from 35 to 75, from 35 to 70, from 35 to 65, from 35 to 60, from 35 to 55, from 35 to 50, from 35 to 45, from 35 to 40, from 40 to 90, from 40 to 85, from 40 to 80, from 40 to 75, from 40 to 70, from 40 to 65, from 40 to 60, from 40 to 55, from 40 to 50, from 40 to 45, from 45 to 90, from 45 to 85, from 45 to 80, from 45 to 75, from 45 to 70, from 45 to 65, from 45 to 60, from 45 to 55, from 45 to 50, from 50 to 90, from 50 to 85, from 50 to 80, from 50 to 75, from 50 to 70, from 50 to 65, from 50 to 60, from 50 to 55, from 55 to 90, from 55 to 85, from 55 to 80, from 55 to 75, from 55 to 70, from 55 to 65, from 55 to 60, from 60 to 90, from 60 to 85, from 60 to 80, from 60 to 75, from 60 to 70, from 60 to 65, from 65 to 90, from 65 to 85, from 65 to 80, from 65 to 75, from 65 to 70, from 70 to 90, from 70 to 85, from 70 to 80, from 70 to 75, from 75 to 90, from 75 to 85, from 75 to 80, from 80 to 90, from 80 to 85, or from 85 to 90) weight percent, based on the total combined weight of reactant A, reactant B, and / or reactant C. Non-limiting examples of suitable materials which may be used as reactant C include: mono hydroxy functional polyethers, e.g. poly(ethylene glycol) monomethyl ether, polypropylene glycol) monobutyl ether, poly(ethylene glycol -co- propylene glycol) monobutyl ether, such as part of the Synalox™ product range; polyesters initiated with an alcohol such as hexanol, heptanol, octanol, nonanol, decanol, dodecanol, tetradecanol, 2- ethylhexanol, or a fatty branched alcohol, such as the Isofol product range from Sasol, withmonomers comprising of cyclic esters such as 8-caprolactone, 5-valerolactone, lactide, glycolide; and / or polyether-esters initiated with polyethylene glycol monomethyl ether, with monomers comprising of cyclic esters such as s-caprolactone, 5-valerolactone, lactide, glycolide.

[0065] In certain embodiments, the particulate solid is present in an amount of from 20 to 80 (such as from 25 to 80, from 30 to 80, from 35 to 80, from 40 to 80, from 45 to 80, from 50 to 80, from 55 to 80, from 60 to 80, from 65 to 80, from 70 to 80, from 75 to 80, from 20 to 75, from 25 to 75, from 30 to 75, from 35 to 75, from 40 to 75, from 45 to 75, from 50 to 75, from 55 to 75, from 60 to 75, from 65 to 75, from 70 to 75, from 20 to 70, from 25 to 70, from 30 to 70, from 35 to 70, from 40 to 70, from 45 to 70, from 50 to 70, from 55 to 70, from 60 to 70, from 65 to 70, from 20 to 65, from 25 to 65, from 30 to 65, from 35 to 65, from 40 to 65, from 45 to 65, from 50 to 65, from 55 to 65, from 60 to 65, from 20 to 60, from 25 to 60, from 30 to 60, from 35 to 60, from 40 to 60, from 45 to 60, from 50 to 60, from 55 to 60, from 20 to 55, from 25 to 55, from 30 to 55, from 35 to 55, from 40 to 55, from 45 to 55, from 50 to 55, from 20 to 50, from 25 to 50, from 30 to 50, from 35 to 50, from 40 to 50, from 45 to 50, from 20 to 45, from 25 to 45, from 30 to 45, from 35 to 45, from 40 to 45, from 20 to 40, from 25 to 40, from 30 to 40, from 35 to 40, from 20 to 35, from 25 to 35, from 30 to 35, from 20 to 30, from 25 to 30, or from 20 to 25) weight percent, based on the total weight of the thermoset composition. The particulate solid may be any solid material suitable for incorporation into a thermosetting resin, such as to create a composite material. Particulate solids of varying densities may be included in thermosetting resins, depending on the intended use of the resulting composition and / or the desired properties of the resulting composition. As such, the percent by weight of the particulate solid present in the composition may vary widely based upon both the density and the amount of particulate solid present.

[0066] In certain embodiments, the particulate solid is present in an amount of from 20 to 80 (such as from 25 to 80, from 30 to 80, from 35 to 80, from 40 to 80, from 45 to 80, from 50 to 80, from 55 to 80, from 60 to 80, from 65 to 80, from 70 to 80, from 75 to 80, from 20 to 75, from 25 to 75, from 30 to 75, from 35 to 75, from 40 to 75, from 45 to 75, from 50 to 75, from 55 to 75, from 60 to 75, from 65 to 75, from 70 to 75, from 20 to 70, from 25 to 70, from 30 to 70, from 35 to 70, from 40 to 70, from 45 to 70, from 50 to 70, from 55 to 70, from 60 to 70, from 65 to 70, from 20 to 65, from 25 to 65, from 30 to 65, from 35 to 65, from 40 to 65, from 45 to 65, from 50 to 65, from 55 to 65, from 60 to 65, from 20 to 60, from 25 to 60, from 30 to 60, from 35 to 60, from 40 to 60, from 45 to 60,from 50 to 60, from 55 to 60, from 20 to 55, from 25 to 55, from 30 to 55, from 35 to 55, from 40 to 55, from 45 to 55, from 50 to 55, from 20 to 50, from 25 to 50, from 30 to 50, from 35 to 50, from 40 to 50, from 45 to 50, from 20 to 45, from 25 to 45, from 30 to 45, from 35 to 45, from 40 to 45, from 20 to 40, from 25 to 40, from 30 to 40, from 35 to 40, from 20 to 35, from 25 to 35, from 30 to 35, from 20 to 30, from 25 to 30, or from 20 to 25) volume percent, based on the total volume of the thermoset composition.

[0067] In certain embodiments, the particulate solid comprises at least one of an extender, a reinforcing material, or a functional filler. Extenders, sometimes referred to as fillers, are generally known to be materials which are included primarily to reduce the cost of the composition without adversely affecting its properties, as they are generally less costly than other ingredients of the composition. In certain embodiments, the extender comprises at least one of calcium carbonate, talc, barium sulfate, alumina, or quartz. Suitable extenders include, but are not limited to: wollastonite (including surface-treated wollastonite); calcium sulfate (as its anhydride, dihydrate or trihydrate); calcium carbonate (including chalk); limestone, marble and synthetic, precipitated calcium carbonates, generally in the form of a ground particulate which often comprises 98+% CaCCh with the remainder being other inorganics such as magnesium carbonate, iron oxide, and aluminosilicates; surface-treated calcium carbonates; talc, including fibrous, modular, needle shaped, and lamellar talc; glass spheres, both hollow and solid; and kaolin, including hard, soft, calcined kaolin, and kaolin comprising various coatings known to the art to facilitate the dispersion in and compatibility with the thermoset resin; mica; feldspar and nepheline syenite; silicate spheres; flue dust; cenospheres; fillite; aluminosilicate (armospheres); natural silica sand; quartz; quartzite; perlite; Tripoli; diatomaceous earth; synthetic silica, and the like.

[0068] Functional fillers are generally known to be materials which are included primarily to provide and / or improve certain properties of the composition, such as fire / flame retardant materials and / or pigments. In certain embodiments, the functional filler comprises at least one of flame retardant materials or pigments. Suitable functional fillers may include, but are not limited to: boron-nitride powder and boron-silicate powders for obtaining cured products having low dielectric constant and low dielectric loss tangent; or silica powder (such as fused silica and / or crystalline silica), alumina, and / or magnesium oxide (or magnesia) for high temperature conductivity.

[0069] In certain embodiments, the extenders and / or functional fillers may comprise particles having an average aspect ratio less than about 5: 1.

[0070] Reinforcing materials are generally known to be materials which are included primarily to increase certain physical properties of the composition, such as tensile strength. In certain embodiments, the reinforcing material comprises at least one type of fibrous material. As used herein, the term “fibrous material” is intended to mean any material of which each particle generally has a length (the longest dimension of each particle of the material, perhaps taken on average) substantially longer than its width (the shortest dimension of each particle the material, perhaps taken on average), such as a ratio of the length to the width of greater than about 5: 1, perhaps taken on average. Suitable fibers may include, but are not limited to, fibers having a high tensile strength (such as greater than 500 kpsi (or 3447 MPa)), carbon or graphite fibers, glass fibers and fibers formed of silicon carbide, alumina, boron, quartz, and the like, as well as fibers formed from organic polymers, such as for example polyolefins, poly(benzothiazole), poly(benzimidazole), polyarylates, poly(benzoxazole), aromatic polyamides, polyaryl ethers and the like, and may include mixtures having two or more such fibers. The fibers may be used in the form of discontinuous or continuous tows made up of multiple filaments, as continuous unidirectional or multidirectional tapes, as chopped loose fibers, or as woven, noncrimped, or nonwoven fabrics. The woven form may be selected from plain, satin, or twill weave style. The noncrimped fabric may have a number of plies and fiber orientations.

[0071] In certain embodiments, the thermosetting resin is present in an amount of from 80 to 20 (such as from 75 to 20, from 70 to 20, from 65 to 20, from 60 to 20, from 55 to 20, from 50 to 20, from 45 to 20, from 40 to 20, from 35 to 20, from 30 to 20, from 25 to 20, from 80 to 25, from 75 to 25, from 70 to 25, from 65 to 25, from 60 to 25, from 55 to 25, from 50 to 25, from 45 to 25, from 40 to 25, from 35 to 25, from 30 to 25, from 80 to 30, from 75 to 30, from 70 to 30, from 65 to 30, from 60 to 30, from 55 to 30, from 50 to 30, from 45 to 30, from 40 to 30, from 35 to 30, from 80 to 35, from 75 to 35, from 70 to 35, from 65 to 35, from 60 to 35, from 55 to 35, from 50 to 35, from 45 to 35, from 40 to 35, from 80 to 40, from 75 to 40, from 70 to 40, from 65 to 40, from 60 to 40, from 55 to 40, from 50 to 40, from 45 to 40, from 80 to 45, from 75 to 45, from 70 to 45, from 65 to 45, from 60 to 45, from 55 to 45, from 50 to 45, from 80 to 50, from 75 to 50, from 70 to 50, from 65 to 50, from 60 to 50, from 55 to 50, from 80 to 50, from 75 to 50, from 70 to 50, from 65 to 50, from 60 to 50, from 80 to 55, from 75 to 55, from 70 to 55, from 65 to 55, from 60 to 55, from 80 to 60, from 75 to 60, from 70 to 60, from 65 to 60, from 80 to 65, from 75 to 65, from 70 to 65, from 80 to 70, from 75 to 70, or from 80 to 75) weight percent, based on the total weight of the thermoset composition.

[0072] In certain embodiments, the thermosetting resin comprises an epoxide resin, an unsaturated polyester resin, a vinyl ester resin, a polyurethane resin, or a phenolic resin. Suitable thermosetting resins include resins which undergo a chemical reaction when heated, catalysed, or subject to ultra-violet, laser light, infra-red, cationic, electron beam, or microwave radiation and become relatively infusible. Illustrative reactions in thermosetting resins include oxidation of unsaturated double bonds, reactions involving epoxy / amine, epoxy / carbonyl, epoxy / hydroxyl, reaction of epoxy with a Lewis acid or Lewis base, polyisocyanate / hydroxy, amino resin / hydroxy moieties, free radical reactions or polyacrylate, cationic polymerization of epoxy resins and vinyl ether and condensation of silanol. Examples of unsaturated resins include polyester resins made by the reaction of one or more diacids or anhydrides with one or more diols. Such resins are commonly supplied as a mixture with a reactive monomer such as styrene or vinyltoluene and are often referred to as orthophthalic resins and isophthalic resins. Further examples include resins using dicyclopentadiene (DCPD) as a co-reactant in the polyester chain. Further examples also include the reaction products of bisphenol A diglycidyl ether with unsaturated carboxylic acids such as methacrylic acid, subsequently supplied as a solution in styrene, commonly referred to as vinyl ester resins. Polymers with hydroxy functionality (such as polyols) are widely used in thermosetting systems to crosslink with amino resins or polyisocyanates. The polyols include acrylic polyols, alkyd polyols, polyester polyols, polyether polyols, and polyurethane polyols. Illustrative amino resins include melamine formaldehyde resins, benzoguanamine formaldehyde resins, urea formaldehyde resins and glycoluril formaldehyde resins. Polyisocyanates are resins with two or more isocyanate groups, including both monomeric aliphatic diisocyanates, monomeric aromatic diisocyanates and their polymers. Illustrative aliphatic diisocyanates include hexamethylene diisocyanate, isophorone diisocyanate and hydrogenated diphenylmethane diisocyanate. Illustrative aromatic isocyanates include toluene diisocyanates and biphenylmethane diisocyanates.

[0073] In certain embodiments, the coupling agent is present in an amount of from 0.5 to 5 (such as from 1 to 5, from 1.5 to 5, from 2 to 5, from 2.5 to 5, from 3 to 5, from 3.5 to 5, from 4 to 5, from 4.5 to 5, from 0.5 to 4.5, from 1 to 4.5, from 1.5 to 4.5, from 2 to 4.5, from 2.5 to 4.5, from 3 to 4.5, from 3.5 to 4.5, from 4 to 4.5, from 0.5 to 4, from 1 to 4, from 1.5 to 4, from 2 to 4, from 2.5 to 4, from 3 to 4, from 3.5 to 4, from 0.5 to 3.5, from 1 to 3.5, from 1.5 to 3.5, from 2 to 3.5, from 2.5 to 3.5, from 3 to 3.5, from 0.5 to 3, from 1 to 3, from 1.5 to 3, from 2 to 3, from 2.5 to 3, from 0.5 to 2.5, from 1 to 2.5, from 1.5 to 2.5, from 2 to2.5, from 0.5 to 2, from 1 to 2, from 1.5 to 2, from 0.5 to 1.5, from 1 to 1.5, or from 0.5 to 1) weight percent, based on the total weight of the thermoset composition.

[0074] In certain embodiments, R2is H. In certain embodiments, R2is COOH.

[0075] In certain embodiments, R3is, independently for each repeat unit, H or CH3. In certain embodiments, R3is, independently for each repeat unit, H or CH2COOH. In certain embodiments, R3is, independently for each repeat unit, CH3 or CH2COOH. In certain embodiments, R3is H. In certain embodiments, R3is CH3. In certain embodiments, R3is CH2COOH.

[0076] In certain embodiments, R4is, independently for each repeat unit, H or a Ci to C36 (such as Ci to C34, Ci to C32, Ci to C30, Ci to C28, Ci to C26, Ci to C24, Ci to C22, Ci to C20, Ci to Cis, Ci to Ci6, Ci to C14, Ci to C12, Ci to C10, Ci to Cs, Ci to Ce, Ci to C4, Ci to C2, C2 to C36, C2 to C34, C2 to C32, C2 to C30, C2 to C28, C2 to C26, C2 to C24, C2 to C22, C2 to C20, C2 to Ci8, C2 to Ci6, C2 to C14, C2 to C12, C2 to C10, C2 to Cs, C2 to Ce, C2 to C4, C4 to C36, C4 to C34, C4 to C32, C4 to C30, C4 to C28, C4 to C26, C4 to C24, C4 to C22, C4 to C20, C4 to Cis, C4 to Cie, C4 to C14, C4 to C12, C4 to C10, C4 to Cs, C4 to Ce, Ce to C36, Ce to C34, Ce to C32, Ce to C30, Ce to C28, Ce to C26, Ce to C24, Ce to C22, Ce to C20, Ce to Cis, Ce to Cie, Ce to C14, Ce to C12, Ce to C10, Ce to Cs, Cs to C36, Cs to C34, Cs to C32, Cs to C30, Cs to C28, Cs to C26, Cs to C24, Cs to C22, Cs to C20, Cs to Cis, Cs to Cie, Cs to C14, Cs to C12, Cs to C10, C10 to C36, C10 to C34, C10 to C32, C10 to C30, C10 to C28, C10 to C26, C10 to C24, C10 to C22, C10 to C20, C10 to Cis, C10 to Cie, C10 to C14, C10 to C12, C12 to C36, C12 to C34, C12 to C32, C12 toC30, C12 to C28, C12 to C26, C12 to C24, C12 to C22, C12 to C20, C12 to C18, C12 to C16, C12 toC14, C14 to C36, C14 to C34, C14 to C32, C14 to C30, C14 tO C28, C14 tO C26, C14 tO C24, C14 tOC22, C14 to C20, C14 to C18, C14 to C16, C16 tO C36, C16 tO C34, C16 tO C32, C16 tO C30, C16 tOC28, C16 tO C26, C16 tO C24, C16 tO C22, C16 tO C20, C16 tO C18, C18 tO C36, C18 tO C34, C18 tOC32, C18 tO C30, C18 tO C28, C18 tO C26, C18 tO C24, C18 tO C22, C18 tO C20, C20 tO C36, C20 tOC34, C20 to C32, C20 to C30, C20 to C28, C20 to C26, C20 to C24, C20 to C22, C22 to C36, C22 toC34, C22 to C32, C22 to C30, C22 to C28, C22 to C26, C22 to C24, C24 to C36, C24 to C34, C24 toC32, C24 to C30, C24 to C28, C24 to C26, C26 to C36, C26 to C34, C26 to C32, C26 to C30, C26 toC28, C28 to C36, C28 to C34, C28 to C32, C28 to C30, C30 to C36, C30 to C34, C30 to C32, C32 toC36, C32 to C34, or C34 to C36) hydrocarbyl group. In certain embodiments, R4is H. In certain embodiments, R4is a Ci hydrocarbyl group. In certain embodiments, R4is a C2 hydrocarbyl group. In certain embodiments, R4is a C4 hydrocarbyl group. In certain embodiments, R4is a Ce hydrocarbyl group. In certain embodiments, R4is a Cs hydrocarbyl group. In certain embodiments, R4is a C10 hydrocarbyl group. In certain embodiments, R4is a C12 hydrocarbyl group. In certain embodiments, R4is a Ci4 hydrocarbyl group. In certain embodiments, R4is a Ci6 hydrocarbyl group. In certain embodiments, R4is a Cis hydrocarbyl group. In certain embodiments, R4is a C20 hydrocarbyl group. In certain embodiments, R4is a C22 hydrocarbyl group. In certain embodiments, R4is a C24 hydrocarbyl group. In certain embodiments, R4is a C26 hydrocarbyl group. In certain embodiments, R4is a C28 hydrocarbyl group. In certain embodiments, R4is a C30 hydrocarbyl group. In certain embodiments, R4is a C32 hydrocarbyl group. In certain embodiments, R4is a C34 hydrocarbyl group. In certain embodiments, R4is a C36 hydrocarbyl group.

[0077] In certain embodiments, R5is, independently for each repeat unit, H or a Ci to C36 (such as Ci to C34, Ci to C32, Ci to C30, Ci to C28, Ci to C26, Ci to C24, Ci to C22, Ci to C20, Ci to Cis, Ci to Ci6, Ci to C14, Ci to C12, Ci to C10, Ci to Cs, Ci to Ce, Ci to C4, Ci to C2, C2 to C36, C2 to C34, C2 to C32, C2 to C30, C2 to C28, C2 to C26, C2 to C24, C2 to C22, C2 to C20, C2 to Cis, C2 to Ci6, C2 to C14, C2 to C12, C2 to C10, C2 to Cs, C2 to Ce, C2 to C4, C4 to C36, C4 to C34, C4 to C32, C4 to C30, C4 to C28, C4 to C26, C4 to C24, C4 to C22, C4 to C20, C4 to Cis, C4 to Cie, C4 to C14, C4 to C12, C4 to C10, C4 to Cs, C4 to Ce, Ce to C36, Ce to C34, Ce to C32, Ce to C30, Ce to C28, Ce to C26, Ce to C24, Ce to C22, Ce to C20, Ce to Cis, Ce to Cie, Ce to C14, Ce to C12, Ce to C10, Ce to Cs, Cs to C36, Cs to C34, Cs to C32, Cs to C30, Cs to C28, Cs to C26, Cs to C24, Cs to C22, Cs to C20, Cs to Cis, Cs to Cie, Cs to C14, Cs to C12, Cs to C10, C10 to C36, C10 to C34, C10 to C32, C10 to C30, C10 to C28, C10 to C26, C10 to C24, C10 to C22, C10 to C20, C10 to Cis, C10 to Cie, C10 to C14, C10 to C12, C12 to C36, C12 to C34, C12 to C32, C12 toC30, C12 to C28, C12 to C26, C12 to C24, C12 to C22, C12 to C20, C12 to C18, C12 to C16, C12 toC14, C14 to C36, C14 to C34, C14 to C32, C14 to C30, C14 tO C28, C14 tO C26, C14 tO C24, C14 tOC22, C14 to C20, C14 to C18, C14 to C16, C16 tO C36, C16 tO C34, C16 tO C32, C16 tO C30, C16 tOC28, C16 tO C26, C16 tO C24, C16 tO C22, C16 tO C20, C16 tO C18, C18 tO C36, C18 tO C34, C18 tOC32, C18 tO C30, C18 tO C28, C18 tO C26, C18 tO C24, C18 tO C22, C18 tO C20, C20 tO C36, C20 tOC34, C20 to C32, C20 to C30, C20 to C28, C20 to C26, C20 to C24, C20 to C22, C22 to C36, C22 toC34, C22 to C32, C22 to C30, C22 to C28, C22 to C26, C22 to C24, C24 to C36, C24 to C34, C24 toC32, C24 to C30, C24 to C28, C24 to C26, C26 to C36, C26 to C34, C26 to C32, C26 to C30, C26 toC28, C28 to C36, C28 to C34, C28 to C32, C28 to C30, C30 to C36, C30 to C34, C30 to C32, C32 toC36, C32 to C34, or C34 to C36) hydrocarbyl group. In certain embodiments, R5is H. In certain embodiments, R5is a Ci hydrocarbyl group. In certain embodiments, R5is a C2 hydrocarbyl group. In certain embodiments, R5is a C4 hydrocarbyl group. In certain embodiments, R5is a Ce hydrocarbyl group. In certain embodiments, R5is a Cs hydrocarbylgroup. In certain embodiments, R5is a Cio hydrocarbyl group. In certain embodiments, R5is a C12 hydrocarbyl group. In certain embodiments, R5is a Ci4 hydrocarbyl group. In certain embodiments, R5is a Ci6 hydrocarbyl group. In certain embodiments, R5is a Cis hydrocarbyl group. In certain embodiments, R5is a C20 hydrocarbyl group. In certain embodiments, R5is a C22 hydrocarbyl group. In certain embodiments, R5is a C24 hydrocarbyl group. In certain embodiments, R5is a C26 hydrocarbyl group. In certain embodiments, R5is a C28 hydrocarbyl group. In certain embodiments, R5is a C30 hydrocarbyl group. In certain embodiments, R5is a C32 hydrocarbyl group. In certain embodiments, R5is a C34 hydrocarbyl group. In certain embodiments, R5is a C36 hydrocarbyl group.

[0078] In certain embodiments, n is an integer from 10 to 1400 (such as from 10 to 1300, from 10 to 1200, from 10 to 1100, from 10 to 1000, from 10 to 900, from 10 to 800, from 10 to 700, from 10 to 600, from 10 to 500, from 10 to 400, from 10 to 300, from 10 to 250, from 10 to 200, from 10 to 150, from 10 to 100, from 10 to 90, from 10 to 80, from 10 to 70, from 10 to 60, from 10 to 50, from 10 to 40, from 10 to 30, from 10 to 20, from 20 to 1400, from 20 to 1300, from 20 to 1200, from 20 to 1100 from 20 to 1000, from 20 to 900, from 20 to 800, from 20 to 700, from 20 to 600, from 20 to 500, from 20 to 400, from 20 to 300, from 20 to 250, from 20 to 200, from 20 to 150, from 20 to 100, from 20 to 90, from 20 to 80, from 20 to 70, from 20 to 60, from 20 to 50, from 20 to 40, from 20 to 30, from 30 to 1400, from 30 to 1300, from 30 to 1200, from 30 to 1100 from 30 to 1000, from 30 to 900, from 30 to 800, from 30 to 700, from 30 to 600, from 30 to 500, from 30 to 400, from 30 to 300, from 30 to 250, from 30 to 200, from 30 to 150, from 30 to 100, from 30 to 90, from 30 to 80, from 30 to 70, from 30 to 60, from 30 to 50, from 30 to 40, from 40 to 1400, from 40 to 1300, from 40 to 1200, from 40 to 1100 from 40 to 1000, from 40 to 900, from 40 to 800, from 40 to 700, from 40 to 600, from 40 to 500, from 40 to 400, from 40 to 300, from 40 to 250, from 40 to 200, from 40 to 150, from 40 to 100, from 40 to 90, from 40 to 80, from 40 to 70, from 40 to 60, from 40 to 50, from 50 to 1400, from 50 to 1300, from 50 to 1200, from 50 to 1100 from 50 to 1000, from 50 to 900, from 50 to 800, from 50 to 700, from 50 to 600, from 50 to 500, from 50 to 400, from 50 to 300, from 50 to 250, from 50 to 200, from 50 to 150, from 50 to 100, from 50 to 90, from 50 to 80, from 50 to 70, from 50 to 60, from 60 to 1400, from 60 to 1300, from 60 to 1200, from 60 to 1100 from 60 to 1000, from 60 to 900, from 60 to 800, from 60 to 700, from 60 to 600, from 60 to 500, from 60 to 400, from 60 to 300, from 60 to 250, from 60 to 200, from 60 to 150, from 60 to 100, from 60 to 90, from 60 to 80, from 60 to 70, from 70 to 1400, from 70 to 1300, from 70 to 1200,from 70 to 1100 from 70 to 1000, from 70 to 900, from 70 to 800, from 70 to 700, from 70 to 600, from 70 to 500, from 70 to 400, from 70 to 300, from 70 to 250, from 70 to 200, from 70 to 150, from 70 to 100, from 70 to 90, from 70 to 80, from 80 to 1400, from 80 to 1300, from 80 to 1200, from 80 to 1100 from 80 to 1000, from 80 to 900, from 80 to 800, from 80 to 700, from 80 to 600, from 80 to 500, from 80 to 400, from 80 to 300, from 80 to 250, from 80 to 200, from 80 to 150, from 80 to 100, from 80 to 90, from 90 to 1400, from 90 to 1300, from 90 to 1200, from 90 to 1100 from 90 to 1000, from 90 to 900, from 90 to 800, from 90 to 700, from 90 to 600, from 90 to 500, from 90 to 400, from 90 to 300, from 90 to 250, from 90 to 200, from 90 to 150, from 90 to 100, from 100 to 1400, from 100 to 1300, from 100 to 1200, from 100 to 1100 from 100 to 1000, from 100 to 900, from 100 to 800, from 100 to 700, from 100 to 600, from 100 to 500, from 100 to 400, from 100 to 300, from 100 to 250, from 100 to 200, from 100 to 150, from 150 to 1400, from 150 to 1300, from 150 to 1200, from 150 to 1100 from 150 to 1000, from 150 to 900, from 150 to 800, from 150 to 700, from 150 to 600, from 150 to 500, from 150 to 400, from 150 to 300, from 150 to 250, from 150 to 200, from 200 to 1400, from 200 to 1300, from 200 to 1200, from 200 to 1100 from 200 to 1000, from 200 to 900, from 200 to 800, from 200 to 700, from 200 to 600, from 200 to 500, from 200 to 400, from 200 to 300, from 200 to 250, from 250 to 1400, from 250 to 1300, from 250 to 1200, from 250 to 1100 from 250 to 1000, from 250 to 900, from 250 to 800, from 250 to 700, from 250 to 600, from 250 to 500, from 250 to 400, from 250 to 300, from 300 to 1400, from 300 to 1300, from 300 to 1200, from 300 to 1100 from 300 to 1000, from 300 to 900, from 300 to 800, from 300 to 700, from 300 to 600, from 300 to 500, from 300 to 400, from 400 to 1400, from 400 to 1300, from 400 to 1200, from 400 to 1100 from 400 to 1000, from 400 to 900, from 400 to 800, from 400 to 700, from 400 to 600, from 400 to 500, from 500 to 1400, from 500 to 1300, from 500 to 1200, from 500 to 1100 from 500 to 1000, from 500 to 900, from 500 to 800, from 500 to 700, from 500 to 600, from 600 to 1400, from 600 to 1300, from 600 to 1200, from 600 to 1100 from 600 to 1000, from 600 to 900, from 600 to 800, from 600 to 700, from 700 to 1400, from 700 to 1300, from 700 to 1200, from 700 to 1100 from 700 to 1000, from 700 to 900, from 700 to 800, from 800 to 1400, from 800 to 1300, from 800 to 1200, from 800 to 1100 from 800 to 1000, from 800 to 900, from 900 to 1400, from 900 to 1300, from 900 to 1200, from 900 to 1100 from 900 to 1000, from 1000 to 1400, from 1000 to 1300, from 1000 to 1200, from 1000 to 1100, from 1100 to 1400, from 1100 to 1300, from 1100 to 1200, from 1200 to 1400, from 1200 to 1300, or from 1300 to 1400).

[0079] In certain embodiments, m is 0 or an integer from 1 to 140 (such as from 1 to 130, from 1 to 120, from 1 to 110, from 1 to 100, from 1 to 90, from 1 to 80, from 1 to 70, from 1 to 60, from 1 to 50, from 1 to 40, from 1 to 30, from 1 to 25, from 1 to 20, from 1 to 15, from 1 to 10, from 1 to 9, from 1 to 8, from 1 to 7, from 1 to 6, from 1 to 5, from 1 to 4, from 1 to 3, from 1 to 2, from 2 to 140, from 2 to 130, from 2 to 120, from 2 to 110 from 2 to 100, from 2 to 90, from 2 to 80, from 2 to 70, from 2 to 60, from 2 to 50, from 2 to 40, from 2 to 30, from 2 to 25, from 2 to 20, from 2 to 15, from 2 to 10, from 2 to 9, from 2 to 8, from 2 to 7, from 2 to 6, from 2 to 5, from 2 to 4, from 2 to 3, from 3 to 140, from 3 to 130, from 3 to 120, from 3 to 110 from 3 to 100, from 3 to 90, from 3 to 80, from 3 to 70, from 3 to 60, from 3 to 50, from 30 to 40, from 3 to 30, from 3 to 25, from 3 to 20, from 3 to 15, from 3 to 10, from 3 to 9, from 3 to 8, from 3 to 7, from 3 to 6, from 3 to 5, from 3 to 4, from 4 to 140, from 4 to 130, from 4 to 120, from 4 to 110 from 4 to 100, from 4 to 90, from 4 to 80, from 4 to 70, from 4 to 60, from 4 to 50, from 4 to 40, from 4 to 30, from 4 to 25, from 4 to 20, from 4 to 15, from 4 to 10, from 4 to 9, from 4 to 8, from 4 to 7, from 4 to 6, from 4 to 5, from 5 to 140, from 5 to 130, from 5 to 120, from 5 to 110 from 5 to 100, from 5 to 90, from 5 to 80, from 5 to 70, from 5 to 60, from 5 to 50, from 5 to 40, from 5 to 30, from 5 to 25, from 5 to 20, from 5 to 15, from 5 to 10, from 5 to 9, from 5 to 8, from 5 to 7, from 5 to 6, from 6 to 140, from 6 to 130, from 6 to 120, from 6 to 110 from 6 to 100, from 6 to 90, from 6 to 80, from 6 to 70, from 6 to 60, from 6 to 50, from 6 to 40, from 6 to 30, from 6 to 25, from 6 to 20, from 6 to 15, from 6 to 10, from 6 to 9, from 6 to 8, from 6 to 7, from 7 to 140, from 7 to 130, from 7 to 120, from 7 to 110 from 7 to 100, from 7 to 90, from 7 to 80, from 7 to 70, from 7 to 60, from 7 to 50, from 7 to 40, from 7 to 30, from 7 to 25, from 7 to 20, from 7 to 15, from 7 to 10, from 7 to 9, from 7 to 8, from 8 to 140, from 8 to 130, from 8 to 120, from 8 to 110 from 8 to 100, from 8 to 90, from 8 to 80, from 8 to 70, from 8 to 60, from 8 to 50, from 8 to 40, from 8 to 30, from 8 to 25, from 8 to 20, from 8 to 15, from 8 to 10, from 8 to 9, from 9 to 140, from 9 to 130, from 9 to 120, from 9 to 110 from 9 to 100, from 9 to 90, from 9 to 80, from 9 to 70, from 9 to 60, from 9 to 50, from 9 to 40, from 9 to 30, from 9 to 25, from 9 to 20, from 9 to 15, from 9 to 10, from 10 to 140, from 10 to 130, from 10 to 120, from 10 to 110 from 10 to 100, from 10 to 90, from 10 to 80, from 10 to 70, from 10 to 60, from 10 to 50, from 10 to 40, from 10 to 30, from 10 to 25, from 10 to 20, from 10 to 15, from 15 to 140, from 15 to 130, from 15 to 120, from 15 to 110 from 15 to 100, from 15 to 90, from 15 to 80, from 15 to 70, from 15 to 60, from 15 to 50, from 15 to 40, from 15 to 30, from 15 to 25, from 15 to 20, from 20 to 140, from 20 to 130, from 20 to 120, from 20 to 110 from 20 to 100, from 20 to 90, from 20 to 80, from20 to 70, from 20 to 60, from 20 to 50, from 20 to 40, from 20 to 30, from 20 to 25, from 25 to 140, from 25 to 130, from 25 to 120, from 25 to 110 from 25 to 100, from 25 to 90, from 25 to 80, from 25 to 70, from 25 to 60, from 25 to 50, from 25 to 40, from 25 to 30, from 30 to 140, from 30 to 130, from 30 to 120, from 30 to 110 from 30 to 100, from 30 to 90, from 30 to 80, from 30 to 70, from 30 to 60, from 30 to 50, from 30 to 40, from 40 to 140, from 40 to 130, from 40 to 120, from 40 to 110 from 40 to 100, from 40 to 90, from 40 to 80, from 40 to 70, from 40 to 60, from 40 to 50, from 50 to 140, from 50 to 130, from 50 to 120, from 50 to 110 from 50 to 100, from 50 to 90, from 50 to 80, from 50 to 70, from 50 to 60, from 60 to 140, from 60 to 130, from 60 to 120, from 60 to 110 from 60 to 100, from 60 to 90, from 60 to 80, from 60 to 70, from 70 to 140, from 70 to 130, from 70 to 120, from 70 to 110 from 70 to 100, from 70 to 90, from 70 to 80, from 80 to 140, from 80 to 130, from 80 to 120, from 80 to 110 from 80 to 100, from 80 to 90, from 90 to 140, from 90 to 130, from 90 to 120, from 90 to 110 from 90 to 100, from 100 to 140, from 100 to 130, from 100 to 120, from 100 to 110, from 110 to 140, from 110 to 130, from 110 to 120, from 120 to 140, from 120 to 130, or from 130 to 140).

[0080] In certain embodiments, R7is a Ci to Cis (such as Ci to Ci4, Ci to C13, Ci to C12, Ci to C11, Ci to C10, Ci to C9, Ci to Cs, Ci to C7, Ci to Ce, Ci to Cs, Ci to C4, Ci to C3, Ci to C2, C2 to Cis, C2 to C14, C2 to C13, C2 to C12, C2 to C11, C2 to C10, C2 to C9, C2 to Cs, C2 to C7, C2 to Ce, C2 to Cs, C2 to C4, C2 to C3, C3 to Cis, C3 to C14, C3 to C13, C3 to C12, C3 to C11, C3 to C10, C3 to C9, C3 to Cs, C3 to C7, C3 to Ce, C3 to Cs, C3 to C4, C4 to Cis, C4 to C14, C4 to C13, C4 to C12, C4 to C11, C4 to C10, C4 to C9, C4 to Cs, C4 to C7, C4 to Ce, C4 to Cs, Cs to Cis, Cs to C14, Cs to C13, Cs to C12, Cs to C11, Cs to C10, Cs to C9, Cs to Cs, Cs to C7, Cs to Ce, Ce to Cis, Ce to C14, Ce to C13, Ce to C12, Ce to C11, Ce to C10, Ce to C9, Ce to Cs, Ce to C7, C7 to Cis, C7 to C14, C7 to C13, C7 to C12, C7 to C11, C7 to C10, C7 to C9, C7 to Cs, Cs to Cis, Cs to C14, Cs to C13, Cs to C12, Cs to C11, Cs to C10, Cs to C9, C9 to Cis, C9 to C14, C9 to C13, C9 to C12, C9 to Cll, C9 to C10, C10 to C15, C10 to C14, C10 to C13, C10 to C12, C10 to Cll, Cll to C15, Cll to C14, Cll to C13, Cll to C12, C12 to C15, C12 to C14, C12 tO C13, C13 tO C15, C13 to C14, Ci4 to Ci5, Cl, C2, C3, C4, Cs, Ce, C7, Cs, C9, C1O,C11, C12, C13, C14, or Cis) hydrocarbyl group.

[0081] In certain embodiments, R8is H. In certain embodiments, R8is CH3.

[0082] In certain embodiments, R9is a Ci to C4 (such as Ci to C3, Ci to C2, C2 to C4, C2 to C3, C3 to C4, Ci, C2, C3, or C4) hydrocarbyl group.

[0083] In certain embodiments, z is an integer from 10 to 80, such as from 10 to 70, from 10 to 60, from 10 to 50, from 10 to 40, from 10 to 30, from 10 to 20, from 20 to 80,from 20 to 70, from 20 to 60, from 20 to 50, from 20 to 40, from 20 to 30, from 30 to 80, from 30 to 70, from 30 to 60, from 30 to 50, from 30 to 40, from 40 to 80, from 40 to 70, from 40 to 60, from 40 to 50, from 50 to 80, from 50 to 70, from 50 to 60, from 60 to 80, from 60 to 70, or from 70 to 80.

[0084] In certain embodiments, R10is a Ci to Cso (such as Ci to C45, Ci to C40, Ci to C35, Ci to C30, Ci to C25, Ci to C20, Ci to Cis, Ci to Ci6, Ci to C14, Ci to C12, Ci to C10, Ci to C9, Ci to Cs, Ci to C7, Ci to Ce, Ci to Cs, Ci to C4, Ci to C3, Ci to C2, C2 to C50, C2 to C45, C2 tO C40, C2 tO C35, C2 tO C30, C2 tO C25, C2 tO C20, C2 tO C18, C2 tO C16, C2 to C14, C2 to C12, C2 to C10, C2 to C9, C2 to Cs, C2 to C7, C2 to Ce, C2 to Cs, C2 to C4, C2 to C3, C3 to C50, C3 to C45, C3 to C40, C3 to C35, C3 to C30, C3 to C25, C3 to C20, C3 to C18, C3 to C16, C3 to C14, C3 to C12, C3 to C10, C3 to C9, C3 to Cs, C3 to C7, C3 to Ce, C3 to Cs, C3 to C4, C4 to Cso, C4 to C45, C4 to C40, C4 to C35, C4 to C30, C4 to C25, C4 to C20, C4 to C18, C4 to C16, C4 to C14, C4 tO C12, C4 to C10, C4 to C9, C4 to Cs, C4 to C7, C4 to Ce, C4 to Cs, Cs to Cso, Cs to C45, Cs to C40, Cs tO C35, Cs tO C30, Cs tO C25, Cs tO C20, Cs tO C18, Cs to C16, Cs to C14, Cs to C12, Cs to C10, Cs to C9, Cs to Cs, Cs to C7, Cs to Ce, Ce to Cso, Ce to C45, Ce to C40, Ce to C35, Ce to C30, Ce to C25, Ce to C20, Ce to Cis, Ce to Cie, Ce to C14, Ce to C12, Ce to C10, Ce to C9, Ce to Cs, Ce to C7, C7 to Cso, C7 to C45, C7 to C40, C7 to C35, C7 to C30, C7 to C25, C7 to C20, C7 to C18, C7 to Cie, C7 to C14, C7 to C12, C7 to C10, C7 to C9, C7 to Cs, Cs to Cso, Cs to C45, Cs to C40, Cs to C35, Cs to C30, Cs to C25, Cs to C20, Cs to Cis, Cs to Cie, Cs to C14, Cs to C12, Cs to C10, Cs to C9, C9 to Cso, C9 to C45, C9 to C40, C9 to C35, C9 to C30, C9 to C25, C9 to C20, C9 to C18, C9 to Cie, C9 to C14, C9 to C12, C9 to C10, C10 to Cso, C10 to C45, C10 to C40, C10 to C35, C10 to C30, C10 to C25, C10 to C20, C10 to Cis, C10 to Cie, C10 to C14, C10 to C12, C12 to Cso, C12 to C45, C12 to C40, C12 to C35, C12 to C30, C12 to C25, C12 to C20, C12 to C18, C12 to C16, C12 to C14, C14 to C50, C14 to C45, C14 to C40, C14 to C35, C14 to C30, C14 tO C25, C14 tO C20, C14 tO C18, C14 tOC16, C16 tO C50, C16 tO C45, C16 tO C40, C16 tO C35, C16 tO C30, C16 tO C25, C16 tO C20, C16 tOC18, C18 tO C50, C18 tO C45, C18 tO C40, C18 tO C35, C18 tO C30, C18 tO C25, C18 tO C20, C20 tOCso, C20 to C45, C20 to C40, C20 to C35, C20 to C30, C20 to C25, C25 to Cso, C25 to C45, C25 toC40, C25 to C35, C25 to C30, C30 to Cso, C30 to C45, C30 to C40, C30 to C35, C35 to Cso, C35 toC45, C35 to C40, C40 to Cso, C45 to Cso, C45 to Cso, Cl, C2, C3, C4, Cs, C6, C7, C8, C9, C10, C12, C14, Cie, Cis, C20, C25, C30, C35, C40, C45, or Cso) hydrocarbyl group.

[0085] In certain embodiments, R11is H. In certain embodiments, R11is CH3.

[0086] In certain embodiments, R12is, independently for each repeat unit, a Ci to Cs(such as Ci to C4, Ci to C3, Ci to C2, C2 to Cs, C2 to C4, C2 to C3, C3 to Cs, C3 to C3, C4 to Cs, Ci, C2, C3, C4, or Cs) hydrocarbyl group.

[0087] In certain embodiments, x is 0 or an integer from 1 to 50, such as from 1 to 40, from 1 to 30, from 1 to 20, from 1 to 15, from 1 to 10, from 1 to 9, from 1 to 8, from 1 to 7, from 1 to 6, from 1 to 5, from 1 to 4, from 1 to 3, from 1 to 2, from 2 to 50, from 2 to 40, from 2 to 30, from 2 to 20, from 2 to 15, from 2 to 10, from 2 to 9, from 2 to 8, from 2 to 7, from 2 to 6, from 2 to 5, from 2 to 4, from 2 to 3, from 3 to 50, from 3 to 40, from 3 to 30, from 3 to 20, from 3 to 15, from 3 to 10, from 3 to 9, from 3 to 8, from 3 to 7, from 3 to 6, from 3 to 5, from 3 to 4, from 4 to 50, from 4 to 40, from 4 to 30, from 4 to 20, from 4 to 15, from 4 to 10, from 4 to 9, from 4 to 8, from 4 to 7, from 4 to 6, from 4 to 5, from 5 to 50, from 5 to 40, from 5 to 30, from 5 to 20, from 5 to 15, from 5 to 10, from 5 to 9, from 5 to 8, from 5 to 7, from 5 to 6, from 6 to 50, from 6 to 40, from 6 to 30, from 6 to 20, from 6 to 15, from 6 to 10, from 6 to 9, from 6 to 8, from 6 to 7, from 7 to 50, from 7 to 40, from 7 to 30, from 7 to 20, from 7 to 15, from 7 to 10, from 7 to 9, from 7 to 8, from 8 to 50, from 8 to 40, from 8 to 30, from 8 to 20, from 8 to 15, from 8 to 10, from 8 to 9, from 9 to 50, from 9 to 40, from 9 to 30, from 9 to 20, from 9 to 15, from 9 to 10, from 10 to 50, from 10 to 40, from 10 to 30, from 10 to 20, from 10 to 15, from 15 to 50, from 15 to 40, from 15 to 30, from 15 to 20, from 20 to 50, from 20 to 40, from 20 to 30, from 30 to 50, from 30 to 40, or from 40 to 50.

[0088] In certain embodiments, y is 0 or an integer from 1 to 20 (such as from 1 to 15, from 1 to 10, from 1 to 8, from 1 to 6, from 1 to 5, from 1 to 4, from 1 to 3, from 1 to 2, from 2 to 20, from 2 to 15, from 2 to 10, from 2 to 8, from 2 to 6, from 2 to 5, from 2 to 4, from 2 to 3, from 3 to 20, from 3 to 15, from 3 to 10, from 3 to 8, from 3 to 6, from 3 to 5, from 3 to 4, from 4 to 20, from 4 to 15, from 4 to 10, from 4 to 8, from 4 to 6, from 4 to 5, from 5 to 20, from 5 to 15, from 5 to 10, from 5 to 8, from 5 to 6, from 6 to 20, from 6 to 15, from 6 to 10, from 6 to 8, from 8 to 20, from 8 to 15, from 8 to 10, from 10 to 20, from 10 to 15, or from 15 to 20).

[0089] In certain embodiments, the sum of x and y is at least 3, such as at least 4, or at least 5.

[0090] Also provided is a method of manufacturing the thermoset composition(s) described herein, comprising dissolving the coupling agent into the thermoset resin with or without solvent, then adding the particulate solid and other additives. The other additives may include at least one of dispersants, defoamers, internal release agents, accelerators, etc.

[0091] Also provided is a method of manufacturing the thermoset composition(s) described herein, comprising dispersing the coupling agent as a dry solid into the thermosetting resin, then adding the particulate solid and other additives. The otheradditives may include at least one of dispersants, defoamers, internal release agents, accelerators, etc.

[0092] Also provided is a method of imparting high / improved interfacial shear strength (tested as described below) to the thermoset composition(s) described herein, comprising dispersing the particulate solid into the thermosetting resin in the presence of the coupling agent.

[0093] Also provided is a method of imparting fire retardancy to the thermoset composition(s) described herein, comprising dispersing the particulate solid (which imparts fire retardancy) into the thermosetting resin in the presence of the coupling agent.

[0094] Also provided is a method of light-weighting the thermoset composition(s) described herein, comprising dispersing a hollow particle (glass sphere) and filler (as the particulate solid) into the thermosetting resin in the presence of the coupling agent.

[0095] Also provided is a method of manufacturing the thermoset composition(s) described herein, comprising treating the particulate solid with the coupling agent to create a treated particulate solid, then adding the treated particulate solid to the thermosetting resin. For example, fibrous material may be pre-treated with a sizing agent that also acts as the coupling agent.

[0096] The subject matter disclosed herein may be better understood with reference to the following examples, which are set forth merely to further illustrate the subject matter disclosed herein. The illustrative examples should not be construed as limiting the subject matter in any manner.

[0097] Example 1 : Carbosperse K752 (45 parts, poly acrylic acid MW 2000 63% active in water ex Lubrizol) was heated to 70 °C under nitrogen and Surfonamine L207 (80.78 parts, a MW 2000 mono-amine terminated polyether EO / PO 33 / 10 ex Huntsman) was added. The temperature was increased to 90 °C for 1 hour, then to 140 °C to remove water over 4 hours. The temperature was then increased to 180 °C for 20.5 hours. An amber liquid was obtained with acid value of 73.7 mg KOH g'1. Molecular weight as determined by gel permeation chromatography in THF spiked with 1% acetic acid against polystyrene standards: Mn = 6471 and Mw = 9654.

[0098] This additive was treated into a stock solution of epoxy resin Araldite LY564 (ex Huntsman) and hardener Aradur 2954 (ex Evonik) at 1.8 parts additive into 50 parts resin to 17.5 part hardener by weight. The stock formulation was thoroughly mixed with a glass rod for 8-10 minutes to ensure the mixture was homogeneous. This stock formulation was then used to position resin formulation beads onto individualglass fibers. These fibers were separated from 600 tex E-glass Hybon™ 2001 continuous roving (ex Nippon Electric Glass). In some instances (Uncleaned Fiber), these separated fibers were used as received (silane sizing) (Average fiber diameter = 12.59 ± 0.81pm, single fiber tensile strength = 2020±437 MPa). In other instances (Cleaned Fiber), these fibers were cleaned and desized by dipping in acetone and sonicating for 50mins at 40°C using a bath sonicator. The fibers were then rinsed gently with de-ionised water and dried at rt (Average fiber diameter = 12.08 ± 0.71 m, single fiber tensile strength = 1657 ± 306 MPa).

[0099] The droplets were applied aiming for a droplet length of 200 pm. Each fiber with droplet positioned was then affixed to a paper frame with small rectangular cutout window. This was to allow easy alignment during testing. Each droplet was then measured using a Keyence digital microscope (VHX-5000F, U.K.) with 200X magnification (1000X magnification was used to measure the fiber diameter. Only well-shaped, symmetrical droplets were considered for the experiments. Maximum droplet length was calculated using equation (1):where Leis the maximum droplet length, 6f is the tensile strength of the fiber, Df is the fiber diameter, and Tuit is the interfacial shear strength (“IFSS”).

[0100] Each mounted and prepared bead on fiber was tested using a single fiber micro bond test to determine the IFSS. Approximately 20-30 repeats were conducted per example to ensure an appropriate IFSS was measured. The micro bond test was conducted using an Instron Universal Testing machine with a load cell of 10N. A customised blade micrometre controlled by a micrometre head and another identical thickness knife edge were used as the bottom grip zone for the microbonds. The microbond tests were conducted with a free distance between the fiber and knife edge of 20-30pm. The test was carried out with a O. lmm / min cross-head speed. In the first stage, the single paper window with resin droplet was mounted and gripped on the top jaw of the testing machine. In the second stage, the paper window frames were cut in such a way that the single fiber with droplet was hung free. At the final stage, the micrometre blades are nearly closed with a gap between them were 20-30pm. This gap constrains the droplet within the knife edges but allows the single fiber to move through freely. The load-displacement curve for each test was recorded to obtain the peak load, Fmax, which, along with the corresponding fiber diameter and embeddedlength, was used to calculate the IFSS (“T”) according to Equation (2). Approximately20-30 single tests were conducted to obtain the average IFSS.

[0101] Example 2: For comparison using the same method above a stock solution of epoxy resin Araldite LY564 (ex Huntsman) and hardener Aradur 2954 (ex Evonik) without any additive was prepared. A ratio of 50 parts resin to 17.5 part hardener by weight was used respectively. The stock formulation was thoroughly mixed with a glass rod for 8-10 minutes to ensure the mixture was homogeneous. The method used for example 1, was then repeated to obtain the IFSS measurement for the un-additised system on the un-cleaned and cleaned glass fibers of the same type.

[0102] Example 3 : For comparison using the same method above a stock solution of epoxy resin Araldite LY564 (ex Huntsman) and hardener Aradur 2954 (ex Evonik) with addition of silane coupling agent - (3 -aminopropyl)tri ethoxy silane was prepared. A ratio of 100 parts resin to 35 parts hardener to 2.1 parts silane by weight was used respectively. The stock formulation was thoroughly mixed with a glass rod for 8-10 minutes to ensure the mixture was homogeneous. The method above was then repeated to obtain the IFSS measurement for the un-additised system on the un-cleaned and cleaned glass fibers of the same type.

[0103] Table 1 details the comparative IFSS (MPa) for example 1 containing system and the example 2 (blank) comparative for both Uncleaned and cleaned Fibers: Table 1

[0104] Except in the Examples, or where otherwise explicitly indicated or required by context, all numerical quantities in this description hereinabove specifying amounts of materials, reaction conditions, molecular weights, number of carbon atoms, and the like, are to be understood as modified by the word “about”. As used herein, the term “about” means that a value of a given quantity is within a range of the explicitly-described value which would be understood by those of ordinary skill, based on the disclosures provided herein, toperform substantially similarly to compositions including the literal amounts described herein.

[0105] It is to be understood that the upper and lower amount, range, and ratio limits set forth hereinabove may be independently combined, and that any amount within a disclosed range is contemplated to provide a minimum or maximum of a narrower range in alternative embodiments (with the proviso, of course, that the minimum amount of a range must be lower than the maximum amount of the same range). Similarly, the ranges and amounts for each element of the subject matter disclosed herein may be used together with ranges or amounts for any of the other elements.

[0106] While certain representative embodiments and details have been shown for the purpose of illustrating the subj ect matter disclosed herein, it will be apparent to those skilled in this art that various changes and modifications may be made therein without departing from the scope of the subject matter. In this regard, the scope of the invention is to be limited only by the following claims.

Claims

What is claimed is:

1. A thermoset composition comprising a dispersion of a particulate solid into a thermosetting resin in the presence of a coupling agent comprising a reaction product of at least a reactant A, with a reactant B and / or a reactant C; wherein the reactant A is represented by the following general formula (A):wherein, independently for each molecule of the reactant A:R1is a terminal group;R2is, independently for each repeat unit, H or COOH;R3is, independently for each repeat unit, H, CH3, or CH2COOH;R4is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group;R5is, independently for each repeat unit, H or a Ci to C36 hydrocarbyl group;R6is a terminal group; n is an integer from 10 to 1400; and m is 0 or an integer from 1 to 140; wherein, when R2is COOH in a repeat unit, R3is H or CH3 in the repeat unit; and wherein, if m is not 0, n is at least 10 times greater than m; wherein the reactant B is represented by the following general formula (B):wherein, independently for each molecule of the reactant B:R7is a Ci to C15 hydrocarbyl group;R8is, independently for each repeat unit, H or CH3;R9is a Ci to C4 hydrocarbyl group; and z is an integer from 10 to 80; wherein the reactant C is represented by the following general formula (C):wherein, independently for each molecule of the reactant C:R10is a Ci to C50 hydrocarbyl group;R11is, independently for each repeat unit, H or CH3;R12is, independently for each repeat unit, a Ci to Cs hydrocarbyl group; x is 0 or an integer from 1 to 50; and y is 0 or an integer from 1 to 20; wherein the sum of x and y is at least 3; wherein substantially all individual molecules of reactant C react with one acid group present in reactant A to form an ester, and / or substantially all individual molecules of reactant B react with (i) one acid group present in reactant A to form an amide, or (ii) two acid groups present in reactant A to form an imide; and wherein the reactant A is present in an amount of from 10 to 65 weight percent, the reactant B is present in an amount of from 0 to 90 weight percent, and the reactant C is present in an amount of from 0 to 90 weight percent, with the proviso that at least one of reactant B or reactant C is present in an amount greater than 0 weight percent, all based on the total combined weight of reactant A, reactant B, and / or reactant C.

2. The thermoset composition of claim 1, wherein the particulate solid is present in an amount of from 20 to 80 weight percent, based on the total weight of the thermoset composition.

3. The thermoset composition of either claim 1 or claim 2, wherein the particulate solid comprises at least one of an extender, a reinforcing material, or a functional filler.

4. The thermoset composition of claim 3, wherein the reinforcing material comprises at least one type of fibrous material.

5. The thermoset composition of any one of claims 1 to 4, wherein the thermosetting resin is present in an amount of from 80 to 20 weight percent, based on the total weight of the thermoset composition.

6. The thermoset composition of any one of claims 1 to 5, wherein the thermosetting resin comprises an epoxide resin, an unsaturated polyester resin, a vinyl ester resin, a polyurethane resin, or a phenolic resin.

7. The thermoset composition of any one of claims 1 to 6, wherein the coupling agent is present in an amount of from 0.5 to 5 weight percent, based on the total weight of the thermoset composition.

8. The thermoset composition of any one of claims 1 to 7, wherein R2is H.

9. The thermoset composition of any one of claims 1 to 8, wherein R3is H.

10. The thermoset composition of any one of claims 1 to 9, wherein n is an integer from 20 to 150.

11. The thermoset composition of any one of claims 1 to 10, wherein m is 0.

12. The thermoset composition of any one of claims 1 to 11, wherein z is an integer from 20 to 50.

13. The thermoset composition of any one of claims 1 to 12, wherein x is 0 and y is an integer from 3 to 20.

14. The thermoset composition of any one of claims 1 to 12, wherein x is an integer from 3 to 50 and y is 0.

15. The thermoset composition of any one of claims 1 to 12, wherein x is an integer from 1 to 50 and y is an integer from 1 to 20.

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